US10457842B2 - Curable composition - Google Patents
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- US10457842B2 US10457842B2 US14/767,182 US201414767182A US10457842B2 US 10457842 B2 US10457842 B2 US 10457842B2 US 201414767182 A US201414767182 A US 201414767182A US 10457842 B2 US10457842 B2 US 10457842B2
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- United States
- Prior art keywords
- curable composition
- film
- weight
- resin
- curable
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000002313 adhesive film Substances 0.000 claims abstract description 50
- 239000000126 substance Substances 0.000 claims abstract description 33
- 239000003822 epoxy resin Substances 0.000 claims description 55
- 229920000647 polyepoxide Polymers 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 229920005989 resin Polymers 0.000 claims description 39
- 239000011347 resin Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 38
- 239000004840 adhesive resin Substances 0.000 claims description 35
- 229920006223 adhesive resin Polymers 0.000 claims description 35
- 239000012855 volatile organic compound Substances 0.000 claims description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
- -1 halogen ions Chemical class 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 25
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 3
- 239000013034 phenoxy resin Substances 0.000 claims description 3
- 229920006287 phenoxy resin Polymers 0.000 claims description 3
- 238000010926 purge Methods 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000004292 cyclic ethers Chemical group 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000686 lactone group Chemical group 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000006056 electrooxidation reaction Methods 0.000 abstract description 7
- 239000010408 film Substances 0.000 description 82
- 239000000463 material Substances 0.000 description 22
- 239000002250 absorbent Substances 0.000 description 19
- 230000002745 absorbent Effects 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 230000008569 process Effects 0.000 description 18
- 238000000576 coating method Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000003825 pressing Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 239000008393 encapsulating agent Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000000642 dynamic headspace extraction Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229940032007 methylethyl ketone Drugs 0.000 description 4
- 239000004843 novolac epoxy resin Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011573 trace mineral Substances 0.000 description 3
- 235000013619 trace mineral Nutrition 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- XGDRLCRGKUCBQL-UHFFFAOYSA-N 1h-imidazole-4,5-dicarbonitrile Chemical compound N#CC=1N=CNC=1C#N XGDRLCRGKUCBQL-UHFFFAOYSA-N 0.000 description 2
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
- CXMYWOCYTPKBPP-UHFFFAOYSA-N 3-(3-hydroxypropylamino)propan-1-ol Chemical compound OCCCNCCCO CXMYWOCYTPKBPP-UHFFFAOYSA-N 0.000 description 2
- GMTAWLUJHGIUPU-UHFFFAOYSA-N 4,5-diphenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GMTAWLUJHGIUPU-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SGUXGJPBTNFBAD-UHFFFAOYSA-L barium iodide Chemical compound [I-].[I-].[Ba+2] SGUXGJPBTNFBAD-UHFFFAOYSA-L 0.000 description 2
- 229910001638 barium iodide Inorganic materials 0.000 description 2
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- PRJKNHOMHKJCEJ-UHFFFAOYSA-N imidazol-4-ylacetic acid Chemical compound OC(=O)CC1=CN=CN1 PRJKNHOMHKJCEJ-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
- AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000007781 pre-processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910001631 strontium chloride Inorganic materials 0.000 description 2
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 1
- PJQDAZJHAYTROB-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole;hydron;bromide Chemical compound Br.C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 PJQDAZJHAYTROB-UHFFFAOYSA-N 0.000 description 1
- UCOSRTUSVXHIMK-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanamine Chemical compound C1=CC=C2NC(CN)=NC2=C1 UCOSRTUSVXHIMK-UHFFFAOYSA-N 0.000 description 1
- IAJLTMBBAVVMQO-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanol Chemical compound C1=CC=C2NC(CO)=NC2=C1 IAJLTMBBAVVMQO-UHFFFAOYSA-N 0.000 description 1
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 1
- ZEVWQFWTGHFIDH-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CNC=1C(O)=O ZEVWQFWTGHFIDH-UHFFFAOYSA-N 0.000 description 1
- JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical compound BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- QXFRVXGMBKPXTF-UHFFFAOYSA-N 2-(2-amino-1h-imidazol-5-yl)acetamide Chemical compound NC(=O)CC1=CN=C(N)N1 QXFRVXGMBKPXTF-UHFFFAOYSA-N 0.000 description 1
- IJJZWCLKTQOUDB-UHFFFAOYSA-N 2-(4-amino-1H-imidazol-5-yl)acetamide hydrochloride Chemical compound Cl.NC=1N=CNC1CC(=O)N IJJZWCLKTQOUDB-UHFFFAOYSA-N 0.000 description 1
- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-UHFFFAOYSA-N 0.000 description 1
- CKEKFQLHCAZGSP-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzimidazol-5-amine Chemical compound NC1=CC=C2N=C(C(F)(F)F)NC2=C1 CKEKFQLHCAZGSP-UHFFFAOYSA-N 0.000 description 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- SULQOTGFPPFUMG-UHFFFAOYSA-N 2-bromo-4,5-dichloro-1h-imidazole Chemical compound ClC=1N=C(Br)NC=1Cl SULQOTGFPPFUMG-UHFFFAOYSA-N 0.000 description 1
- JLVIHQCWASNXCK-UHFFFAOYSA-N 2-butyl-5-chloro-1h-imidazole-4-carbaldehyde Chemical compound CCCCC1=NC(C=O)=C(Cl)N1 JLVIHQCWASNXCK-UHFFFAOYSA-N 0.000 description 1
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YECSLYXTXWSKBO-UHFFFAOYSA-N 2-nonyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CCCCCCCCC)=NC2=C1 YECSLYXTXWSKBO-UHFFFAOYSA-N 0.000 description 1
- RJIQELZAIWFNTQ-UHFFFAOYSA-N 2-phenyl-1h-imidazole;1,3,5-triazinane-2,4,6-trione Chemical class O=C1NC(=O)NC(=O)N1.C1=CNC(C=2C=CC=CC=2)=N1 RJIQELZAIWFNTQ-UHFFFAOYSA-N 0.000 description 1
- PNACPZXTLQWNTP-UHFFFAOYSA-N 2-phenyl-3h-benzimidazole-5-sulfonic acid;hydrate Chemical compound O.N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 PNACPZXTLQWNTP-UHFFFAOYSA-N 0.000 description 1
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
- JHJHDEZWUNCTQO-UHFFFAOYSA-N 2-prop-2-enylsulfanyl-1h-benzimidazole Chemical compound C1=CC=C2NC(SCC=C)=NC2=C1 JHJHDEZWUNCTQO-UHFFFAOYSA-N 0.000 description 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
- MKBBSFGKFMQPPC-UHFFFAOYSA-N 2-propyl-1h-imidazole Chemical compound CCCC1=NC=CN1 MKBBSFGKFMQPPC-UHFFFAOYSA-N 0.000 description 1
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- LLOAINVMNYBDNR-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydrobenzimidazole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2NC(=S)NC2=C1 LLOAINVMNYBDNR-UHFFFAOYSA-N 0.000 description 1
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
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- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L101/04—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing halogen atoms
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H01L51/0035—
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- H01L51/5253—
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- H01L51/5259—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/846—Passivation; Containers; Encapsulations comprising getter material or desiccants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
Definitions
- the present invention relates to a curable composition, an adhesive film including the same, and an organic electronic device including the same.
- OED Organic electronic device
- OLED are devices including an organic material layer generating a flow of charges using holes and electrons, and for example, include a photovoltaic device, a rectifier, a transmitter, an organic light emitting diode (OLED), and so forth.
- an OLED has less power consumption and a higher response speed, and forms a thinner display device or light than a conventional light source. Further, an OLED has excellent space utilization, and is expected to be applied in a variety of fields including all types of portable devices, monitors, notebook computers and TVs.
- a major problem in extending compatibility and use of OLEDs is durability.
- Organic materials and metal electrodes included in the OLED are too easily oxidized by external factors such as moisture. Therefore, a product including an OLED is very sensitive to environmental factors. Accordingly, there is a need for development of encapsulants to prevent penetration of oxygen or moisture from an external environment with respect to an OED such as an OLED.
- organic volatile substances contained in the encapsulant itself may affect an organic light emitting material or an electrode part, and thus effective control of the organic volatile substances is required.
- the present invention is directed to providing a curable composition capable of effectively controlling moisture, ionic substances, and other foreign substances which enter an organic electronic device, resulting in damage to an element and electrochemical corrosion, and also capable of improving the lifespan and durability of the organic electronic device, and an adhesive film including the curable composition.
- a curable composition and an adhesive film including the same according to an embodiment of the present invention may be applied to encapsulate an entire surface of an organic electronic element of an organic electronic device. Further, the adhesive film may have a single-layered or multilayered structure.
- the term “organic electronic device” denotes a product or device which has an element including an organic material layer generating a flow of charges using holes and electrons between a pair of electrodes opposite to each other, and examples thereof include a photovoltaic device, a rectifier, a transmitter, an organic light emitting diode (OLED), and so forth, but are not limited thereto.
- the organic electronic device may be an OLED.
- an exemplary curable composition which may include a curable adhesive resin, and satisfy the following Equation 1 or 2.
- Equation 1 X ⁇ 1,000 ppm
- Equation 2 Y ⁇ 1,000 ppm
- Equation 1 X is an amount of volatile organic compounds, which is measured by preparing a film with the curable composition, maintaining 50 mg of the film sample at 150° C. for 1 hour, and using purge and trap-gas chromatography/mass spectrometry. Further, in Equation 2, Y is an amount of ionic substances contained in the curable composition, which is obtained by preparing a film with the curable composition, and measuring 50 mg of the film sample according to ASTM D 7359:2008. In an embodiment, a curable composition according to an exemplary embodiment of the present invention may satisfy both of Expressions 1 and 2.
- a moisture content of a film sample formed of the curable composition may be 0.01 wt % or more, and the moisture content of the film sample is measured according to ASTM D3451-06 (2012) (Standard Guide for Testing Coating Powders and Powder Coatings by Coulometric Karl Fischer Titration) after preparing a film with the curable composition, and maintaining 50 mg of the film sample under conditions of 25° C. and a relative humidity of 50% for 24 hours. That is, in Equation 1, X may be a measured amount of volatile organic compounds volatilized from components, which have a moisture content of 0.01 wt % or more as measured after maintaining the film sample of the curable composition under conditions of 25° C.
- X may be an amount of volatile organic compounds volatilized after maintaining the curable composition which satisfies the above conditions at 150° C. for 1 hour (purge and trap).
- the upper limit of the moisture content may be 1 wt % or less, but is not particularly limited.
- the term “component of curable composition” may denote a raw material which is a base of the curable composition.
- the component of the curable composition may be a curable adhesive resin, a curing agent, a silane coupling agent, a high-molecular-weight resin or an organic solvent as will be described below, but is not limited thereto, and is not particularly limited as long as it is a material forming the curable composition.
- the curable composition according to an embodiment of the present invention may control damage to an element by a final composition, by limiting volatile materials contained in substances which may contain moisture indirectly, deliver moisture through volatilization, or be volatilized and damage an organic element. Since moisture may result in the worst damage to the element of the organic electronic device, physical and chemical damage to the organic electronic device may be prevented by controlling moisture.
- X which is an amount of volatile organic compounds
- VOC volatile organic compound
- the amount of a volatile organic compound, which is volatilized through purge and trap after about 50 mg of the film sample is maintained at 150° C. for 1 hour with toluene as a standard reagent may be 1,000 ppm or less, 900 ppm or less, 800 ppm or less, 700 ppm or less, 600 ppm or less, 500 ppm or less, 300 ppm or less, or 200 ppm or less.
- Y which is an amount of ionic substances contained in the curable composition and measured through the ASTM D 7359:2008 measurement method, may be 1,000 ppm or less, 900 ppm or less, 800 ppm or less, 700 ppm or less, 600 ppm or less, or 550 ppm or less.
- physical and chemical damage to the organic electronic device may be prevented by controlling a total amount of the volatile organic compounds and a total amount of the ionic substances contained in the curable composition as described above. More specifically, acid or base ionic substances may cause corrosion of wires in the organic electronic device, thus resulting in electrochemical corrosion of the organic electronic device and occurrence of dark spots.
- volatile organic compound may be defined as all organic compounds present in a gas phase in the atmosphere.
- VOC is a common term used to denote all organic materials which may be present in a gas phase at room temperature and atmospheric pressure such as hydrocarbons composed only of carbon and hydrogen, halogenated hydrocarbons, hydrocarbons containing nitrogen or sulfur, and the like, and may include semi-volatile organic compounds in a broader sense.
- VOCs may denote organic solvents, by-products generated from pyrolysis of a curing agent, by-products generated from an addition reaction, etc.
- purge and trap may denote a VOC-preprocessing device or method, delivering minute amounts of VOCs that are extracted and concentrated during gas chromatography (GC) or gas chromatography/mass spectrometry (GC/MS).
- GC gas chromatography
- GC/MS gas chromatography/mass spectrometry
- GC/MS denotes an analytical device or method for separating and analyzing contents of a solution for various specimens.
- GC/MS includes a combination of GC used to separate a variety of compounds and MS used to measure an atomic mass of a substance entering from GC. Retention time and mass vary depending on types of the compounds. Since GC/MS is connected to computer software storing a library of a specific form of compounds, types of the substances as well as a concentration thereof are identified through comparison with the library in which compounds in a solution may be determined. A successive investigation after determining presence of the compounds is usually performed through GC to analyze a specific material.
- the VOC according to an embodiment of the present invention may be a substance having a vapor pressure of 0.01 psi or more, 0.015 psi or more, 0.02 psi or more, or 0.025 psi or more. Since all materials having a high-vapor pressure and volatility are VOCs, the upper limit of the vapor pressure is not particularly limited, but may be 1 psi or less. Further, the VOC according to an embodiment of the present invention may have a boiling point of 200° C. or less, 150° C. or less, 120° C. or less, 115° C. or less, or 100° C. or less, and the lower limit thereof may be 50° C. or more, but is not particularly limited thereto.
- the term “ionic substance” is not particularly limited as long as the substance is capable of causing wire corrosion of an organic electronic device.
- the ionic substance may be halogen ions, and may be chlorine ions.
- halogen ions may result in electrochemical corrosion of the organic electronic device, and thus damage to the organic electronic device may be prevented by controlling the content of the halogen ions.
- the curable composition includes the curable adhesive resin as described above.
- the curable adhesive resin may be properly selected to satisfy the aforementioned Equation 1 or 2.
- the curable adhesive resin may have a water vapor transmission rate (WVTR) of 50 g/m 2 ⁇ day or less, preferably 30 g/m 2 ⁇ day or less, more preferably 20 g/m 2 ⁇ day or less, and most preferably 15 g/m 2 ⁇ day or less in a cured state.
- WVTR water vapor transmission rate
- cured state of curable adhesive resin denotes that the curable adhesive resin is changed to a state in which the curable adhesive resin may retain components such as moisture absorbents, fillers, and the like, and may exhibit performance as a structural curable composition, as applied as an encapsulant after being cured or cross-linked independently or through a reaction with other components such as a curing agent, or the like.
- the WVTR denotes a WVTR of a curable adhesive resin, and the WVTR is obtained after the curable adhesive resin is cured, formed to be a film type having a thickness of 100 ⁇ m, and measured in a thickness direction of the cured material under conditions of 38° C. and a relative humidity of 100%.
- the lower limit of the WVTR of the curable adhesive resin may be 0 g/m 2 ⁇ day or 0.01 g/m 2 ⁇ day. Penetration of moisture, water vapor, oxygen, or the like into the organic electronic device may be effectively suppressed by controlling the WVTR to be in the above range.
- curable adhesive resin that may be used in the present invention are not particularly limited, and for example, any of various heat-curable or photo-curable resins well known in a related art may be used.
- heat-curable resin denotes a resin which may be cured by properly applying heat or aging
- photo-curable resin denotes an electromagnetic-wave-curable resin.
- microwaves, infrared (IR) rays, ultraviolet (UV) rays, X rays and gamma rays and a particle beam such as an alpha-particle beam, a proton beam, a neutron beam or an electron beam may be included.
- a cationic photo-curable resin may be included.
- the cationic photo-curable resin denotes a resin which may be cured through cationic polymerization or a cationic curing reaction induced by electromagnetic wave radiation.
- the curable adhesive resin may be a dual-curable resin including both heat-curable and photo-curable properties.
- specific types of the curable adhesive resin are not particularly limited as long as the curable adhesive resin has the characteristics described above.
- a resin including one or more heat-curable functional groups such as a glycidyl group, an isocyanate group, a hydroxy group, a carboxyl group, an amide group, or the like, or one or more electromagnetic-wave-curable functional groups such as an epoxide group, a cyclic ether group, a sulfide group, an acetal group, a lactone group, or the like may be included.
- an acryl resin, a polyester resin, an isocyanate resin, an epoxy resin, or the like may be included, but is not limited thereto.
- the curable adhesive resin may be a low-chlorine-grade epoxy resin.
- a high-purity epoxy resin of which a content of halogen ions is decreased may be used, and more specifically, the high-purity epoxy resin having a halogen ion content of 1,000 ppm or less, 800 ppm or less, 600 ppm or less, 500 ppm or less, 400 ppm or less, or 300 ppm or less as measured according to ASTM D 7359:2008 may be used.
- the halogen ions may be chlorine ions.
- the ionic substance such as the halogen ions may cause wire corrosion of the organic electronic element, resulting in electrochemical corrosion of the organic electronic device and generation of dark spots. Accordingly, volatile materials may be inhibited by using the high-purity epoxy resin. Further, in an embodiment, the epoxy resin may be in a liquid phase or a semi-solid phase.
- an aromatic or aliphatic epoxy resin; or a linear or branched epoxy resin may be used as the curable adhesive resin.
- an epoxy resin containing two or more functional groups an epoxy resin having an epoxy equivalent in a range of 180 to 1,000 g/eq may be used. When the epoxy resin having an epoxy equivalent in the above range is used, characteristics of the cured material such as adhesive performance and a glass transition temperature may be effectively maintained.
- Such an epoxy resin may be one or mixtures of at least two of a cresol novolac epoxy resin, a bisphenol A-type epoxy resin, a bisphenol A-type novolac epoxy resin, a phenol novolac epoxy resin, a tetrafunctional epoxy resin, a biphenyl-type epoxy resin, a triphenol methane-type epoxy resin, an alkyl-modified triphenol methane epoxy resin, a naphthalene-type epoxy resin, a dicyclopentadiene-type epoxy resin, or a dicyclopentadiene modified phenol-type epoxy resin.
- an epoxy resin having a ring-shaped structure in its molecular structure may be used, and more preferably, an epoxy resin including an aromatic group (e.g., a phenyl group) may be used.
- an epoxy resin including an aromatic group e.g., a phenyl group
- a cured material may have excellent thermal and chemical stability, and show a low moisture-absorption amount, and thus improve structural reliability of the encapsulant of the organic electronic device.
- aromatic-group-containing epoxy resin may include one or mixtures of at least two of a biphenyl-type epoxy resin, a dicyclopentadiene-type epoxy resin, a naphthalene-type epoxy resin, a dicyclopentadiene modified phenol-type epoxy resin, a cresol-type epoxy resin, a bisphenol-type epoxy resin, a xyloc-type epoxy resin, a multifunctional epoxy resin, a phenol novolac epoxy resin, a triphenol methane-type epoxy resin, an alkyl-modified triphenol methane epoxy resin, or the like, but are not limited thereto.
- a silane-modified epoxy resin preferably, a silane-modified epoxy resin having an aromatic group
- an epoxy resin which is modified with silane and structurally has a silane group is used, adhesion with an inorganic material such as a glass substrate, a substrate, or the like is maximized, and moisture barrier properties, durability, reliability, and so forth may be also improved.
- the use of the silane-modified epoxy resin is effective in minimizing a content of the silane coupling agent which may damage the organic electronic device due to the by-products.
- the silane-modified epoxy resin may be a high-purity epoxy resin in which a content of halogen ions is decreased, and more specifically, may be the silane-modified epoxy resin having the halogen ion content of 1,000 ppm or less, 800 ppm or less, 600 ppm or less, 500 ppm, 400 ppm or less, or 300 ppm or less as measured according to ASTM D 7359:2008. Accordingly, the VOCs described above may be effectively controlled.
- Specific types of the epoxy resin as described above that may be used in the present invention are not particularly limited, for example, the resins described above may be easily purchased from vendors such as Kukdo Chemical Co., Ltd., etc.
- the curable composition according to an embodiment of the present invention may include one or more selected from the group consisting of a curing agent, a silane coupling agent and an organic solvent.
- substances capable of entering the organic electronic device as VOCs, damaging the element, and causing electrochemical corrosion may include organic solvents, and thus generation of trace elements and an organic volatilization amount of the curable composition may be reduced by controlling the organic solvents.
- the boiling point of the organic solvent may be in a range of 100° C. or less, 95° C. or less, 90° C. or less, 85° C. or less, or 80° C. or less, and the lower limit thereof may be 50° C. or more, but is not particularly limited.
- the organic solvent may include hydrocarbon solvents, alcohols, ester compounds, ketones or ether compounds.
- the solvent that may be used in the present invention may include one or mixtures of at least two of methyl ethyl ketone (MEK), acetone, toluene, dimethyl formamide (DMF), methyl cellosolve (MCS), tetra-hydrofuran (THF), N-methyl pyrrolidone (NMP), ethyl cellosolve (ECS), or the like, but is not limited thereto.
- MEK methyl ethyl ketone
- DMF dimethyl formamide
- MCS methyl cellosolve
- THF tetra-hydrofuran
- NMP N-methyl pyrrolidone
- ECS ethyl cellosolve
- the curable composition according to an embodiment of the present invention may further include a curing agent which may form a matrix such as a cross-linked structure or the like by reacting with the curable adhesive resin.
- a curing agent which may form a matrix such as a cross-linked structure or the like by reacting with the curable adhesive resin.
- a specific type of the curing agent that may be used in the present invention is not specifically limited and may be properly selected depending on a used curable adhesive resin or a type of the functional group included in the resin, and particularly, a curing agent having a small amount of by-products or unreacted materials upon VOC analysis is preferable.
- an epoxy resin used as the curable adhesive resin
- an epoxy resin well-known as a curing agent in the related art may be used, and more specifically, one or mixtures of at least two of all sorts of amine-based compounds, imidazole-based compounds, phenol-based compounds, phosphorus-based compounds, acid anhydride-based compounds, or the like may be used without being limited thereto.
- the curing agent may be an imidazole-based compound in order to minimize by-products of the reaction and a reaction temperature.
- the curable composition according to an embodiment of the present invention may include the curing agent at an amount of 0.5 to 20 parts by weight, preferably, 1 to 10 parts by weight with respect to 100 parts by weight of the heat-curable resin.
- the above content is merely one example. That is, a content of the curing agent may be changed according to a type and content of the curable adhesive resin or the functional group, or a matrix structure or crosslinking density to be implemented in an embodiment of the present invention.
- the curing agent preferably generates a small amount of heat-by-products, unreacted materials, or materials formed by an addition reaction upon VOC analysis.
- the curing agent may be an imidazole curing agent which starts to cure at a temperature in a range of 50 to 170° C.
- the imidazole-based compound may include one or more selected from the group consisting of 2-ethyl imidazole, 2-ethyl-4-methylimidazole, 2-aminobenzeneimidazole, 2-amino-4-imidazolecarboxyamide, 2-aminoimidazolesulphate, 2-(trifluoromethyl)benzimidazole, 1-benzimidazole, 4,5-diphenyl-2-imidazolethiol, 2-methyl-5-nitroimidazole, 4-nitroimidazole, 2,4,5-tribromoimidazole, 4-phenylimidazole, 2-(2-pyridyl)benzimidazole, 2-benzimidazolemethanol, 4-amino-5-imidazolecarboxyamide hydrochloride, 2-(aminomethyl)benzimidazole dehydchloride, 5-chloro-2-(trichloromethyl)benzimidazole, 4-methylimidazole, 4-methyl-5-imidazolecarboxyamide
- the curing agent may include a first curing agent which starts to cure at a temperature in a range of 50 to 120° C. and/or a second curing agent which starts to cure at a temperature of more than 120° C. and 170° C. or less. Accordingly, the second curing agent may be separately used.
- processability, storage stability, and a process speed according to a curing speed may be controlled by mixing an intermediate-speed curing agent which starts to cure at about 100° C. and a slow-speed curing agent which starts to cure at about 150° C.
- the curing agent which starts to cure at a temperature of less than 100° C. is used separately, storage stability is reduced and heat stability is decreased in the process.
- the curing agent which starts to cure at the specific temperature as described above degradation of the organic electronic element may be prevented, and volatile components generated by pyrolysis and an addition reaction may be avoided.
- the first curing agent which starts to cure at a temperature in a range of 50 to 120° C. one or more selected from the group consisting of 2-undecylimidazole, 2-heptadecylimidazole(2-heptadecylimidazole), 2-phenylimidazole, 2-phenyl-4-methylimidazole (2-phenyl-4-methylimidazole), 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole and 2-phenylimidazoline may be included.
- the second curing agent which starts to cure at a temperature of more than 120° C. and 170° C. or less, one or more selected from the group consisting of 2-phenyl-4-methyl-5-hydroxyimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium-trimellitate, 2,4-diamino-6 [2′-undecylimidazolyl-(1′)]-ethyl-s-triazine, 2,4-diamino-6-[2′-ethyl-4′-methylimidazolyl-(1′)]-ethyl-s-triazine, 1-cyano-2-phenylimidazolium-trimellitate, 2-phenylimidazole isocyanuric acid adducts, and 1-benzyl-2-phenylimidazole hydrobromide may be included.
- the first curing agent 1-cyan
- the curable composition according to an embodiment of the present invention may further include a curing catalyst.
- the curing catalyst is not limited as long as it generates a small amount of by-products by heat, unreacted materials or materials generated from the addition reaction upon VOC analysis, and for example, a 3-grade amine-based material is preferable.
- the curing catalyst may include one or more selected from the group consisting of triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, tris(dimethylaminomethyl)phenol, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2-heptadecylimidazole.
- the curable composition according to an embodiment of the present invention may further include a silane coupling agent.
- the silane coupling agent increases adhesion and adhesive stability of an adhesive, improves heat resistance and humidity resistance, and also enhances adhesion reliability when subjected to severe conditions for a long time.
- the silane coupling agent since the silane coupling agent generates by-products of the alcohol component by heat, it is preferable to minimize a content of the silane coupling agent within the scope of the object of the present invention.
- silane coupling agent for example, one type or mixtures of at least two types of gamma-glycidoxypropyl triethoxy silane, gamma-glycidoxypropyl trimethoxy silane, gamma-glycidoxypropyl methyldiethoxy silane, gamma-glycidoxypropyl triethoxy silane, 3-mercaptopropyl trimethoxy silane, vinyltrimethoxysilane, vinyltriethoxy silane, gamma-methacryloxypropyl trimethoxy silane, gamma-methacryloxy propyl triethoxy silane, gamma-aminopropyl trimethoxy silane, gamma-aminopropyl triethoxy silane, 3-isocyanato propyl triethoxy silane, gamma-acetoacetatepropyl trimethoxysilane, gamma-acetoacetatepropyl triethoxy si
- the curable composition may include the silane coupling agent in a range of less than 2 parts by weight, 0.01 to 1.9 parts by weight, 0.01 to 1.8 parts by weight, 0.01 to 1.5 parts by weight, or 0.01 to 1.3 parts by weight with respect to 100 parts by weight of the curable adhesive resin.
- the silane coupling agent is included at 2 parts by weight or more, dark spots may occur due to by-products of the alcohol component generated from the silane coupling agent, and bubble-occurrence frequency may increase upon bonding and curing.
- the curable composition according to an embodiment of the present invention may include a moisture absorbent as necessary.
- moisture absorbent may be used as a collective term for components capable of absorbing or removing moisture or water vapor entering from the outside through a physical or chemical reaction. That is, the moisture absorbent denotes a moisture-reactive absorbent or physical absorbent, and mixtures thereof may also be used.
- the moisture-reactive absorbent absorbs moisture or water vapor by chemically reacting with water vapor, moisture or oxygen entering an adhesive film including the curable composition.
- the physical absorbent may lengthen the traveling path of moisture or water vapor penetrating into an encapsulating structure to be described below, thereby suppressing penetration thereof, and may maximize barrier properties with respect to moisture and water vapor through a matrix structure of the curable adhesive resin and interaction with the moisture-reactive absorbent, etc.
- the moisture-reactive absorbent may include one type or mixtures of at least two types of metal powders such as alumina or the like, a metallic oxide, metal salts, phosphorus pentoxide (P 2 O 5 ), or the like, and the physical absorbent may include silica, zeolite, titania, zirconia, montmorillonite, or the like.
- metallic oxide in the above may include, but are not limited, lithium oxide (Li 2 O), sodium oxide (Na 2 O), barium oxide (BaO), calcium oxide (CaO), magnesium oxide (MgO), or the like
- metal salts may include, but are not limited, sulfates such as lithium sulfate (Li 2 SO 4 ), sodium sulfate (Na 2 SO 4 ), calcium sulfate (CaSO 4 ), magnesium sulfate (MgSO 4 ), cobalt sulfate (CoSO 4 ), gallium sulfate (Ga 2 (SO 4 ) 3 ), titanium sulfate (Ti(SO 4 ) 2 ), nickel sulfate (NiSO 4 ), or the like; metal halides such as calcium chloride (CaCl 2 ), magnesium chloride (MgCl 2 ), strontium chloride (SrCl 2 ), yttrium chloride (YCl 3
- the moisture absorbent such as the metallic oxide, or the like
- an adhesive film which is a film type prepared from the aforementioned curable composition, may be formed to have a shape of a thin film having a thickness of 30 ⁇ m or less according to types of the organic electronic device to be applied, and here, a milling process of the moisture absorbent may be required.
- the milling process of the moisture absorbent may include processes such as three roll mill, bead mill, ball mill, etc.
- the curable composition according to an embodiment of the present invention may include the moisture absorbent at an amount in a range of 0 to 100 parts by weight, 1 to 90 parts by weight, 5 to 80 parts by weight, or 10 to 50 parts by weight with respect to 100 parts by weight of the curable adhesive resin.
- a cured material may exhibit superior moisture and water vapor barrier properties by preferably controlling the moisture absorbent content to be included at 5 parts by weight or more. Further, by controlling the moisture absorbent content to be included at 100 parts by weight or less, the cured material may exhibit excellent moisture barrier properties while forming an encapsulating structure of a thin film.
- a unit of “parts by weight” denotes a weight ratio between the components.
- the curable composition according to an embodiment of the present invention may further include a high-molecular-weight resin.
- the high-molecular-weight resin may serve to improve formability. Further, the high-molecular-weight resin may serve as a high-temperature-viscosity control agent controlling flowability in a hot-melting process.
- Examples of the high-molecular-weight resin that may be used in the present invention are not particularly limited as long as the high-molecular-weight resin has compatibility with other components such as the curable adhesive resin, etc. However, when an excess amount of halogen ions is included in the high-molecular-weight resin, the organic electronic element may be affected thereby, and thus a high-purity-low-chlorine grade high-molecular-weight resin may be used.
- the high-molecular-weight resin may include halogen ions at a content of 1,000 ppm or less, 900 ppm or less, 500 ppm or less, 700 ppm or less, 600 ppm or less, or 550 ppm or less as measured according to ASTM D 7359:2008.
- the halogen ions may be chlorine ions.
- the high-molecular-weight resin to be used may include, as a resin having a weight-average molecular weight of 20,000 or more, one or mixtures of at least two of a phenoxy resin, an acrylate resin, a high-molecular-weight epoxy resin, an ultra-high-molecular-weight epoxy resin, a high polarity functional group-containing rubber, and a high polarity functional group containing-reactive rubber, but are not limited thereto.
- a content of the high-molecular-weight resin is controlled depending on desired physical properties, and is not particularly limited.
- the high-molecular-weight resin may be contained at an amount in a range of 20 to 200 parts by weight, preferably 20 to 150 parts by weight, and more preferably 30 to 100 parts by weight with respect to 100 parts by weight of the curable adhesive resin in an embodiment of the present invention.
- compatibility of the resin composition and each component may be effectively maintained, and the resin composition may also function as an adhesive.
- the curable composition according to an embodiment of the present invention may further include additives for improving durability of the cured material, such as a filler, a leveling agent, a dispersant, an antifoamer, a UV stabilizer, and an antioxidant, within a range in which a small amount of by-products by heat, unreacted materials, materials generated from an addition reaction is formed upon VOC analysis.
- additives for improving durability of the cured material such as a filler, a leveling agent, a dispersant, an antifoamer, a UV stabilizer, and an antioxidant
- the present invention also relates to an adhesive film including the curable composition described above.
- a structure of the adhesive film according to an embodiment of the present invention is not particularly limited as long as the adhesive film includes the curable composition, but in an embodiment, the adhesive film may have a structure including a base film or release film (which may hereinafter be referred to as a “first film”); and the curable composition formed on the base film or release film.
- a base film or release film which may hereinafter be referred to as a “first film”
- the adhesive film according to an embodiment of the present invention may further include a base film or release film formed on the curable composition (which may hereinafter be referred to as a “second film”).
- the first film that may be used in the present invention are not particularly limited.
- a typical polymer film in the related art may be used as the first film.
- examples of the base or release film may include a polyethylene terephthalate (PET) film, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a vinyl chloride copolymer film, a polyurethane film, an ethylene-vinyl acetate film, an ethylene-propylene copolymer film, an ethylene-ethyl acetate copolymer film, an ethylene-methyl acetate copolymer film, a polyimide film, or the like.
- PET polyethylene terephthalate
- a release agent used for release treatment of the base film may include alkyd-based, silicone-based, fluorine-based, unsaturated ester-based, polyolefin-based, wax-based release agents, etc.
- alkyd-based, silicone-based, or fluorine-based release agents may be preferably used in terms of heat resistance, but the release agent is not limited thereto.
- types of the second film that may be used in the present invention are not particularly limited either.
- the same type of film as the first film or a different type of film from the first film may be used as the second film within the range in which the first film is exemplified as described above.
- the second film may also be subjected to proper release treatment in an embodiment of the present invention.
- the thickness of the base film or the release film (first film) is not particularly limited, and may be adjusted properly depending on a purpose.
- a thickness of the first film may be in a range of 10 to 500 ⁇ m, preferably 20 to 200 ⁇ m in an embodiment of the present invention.
- the thickness of the first film is less than 10 ⁇ m, the base film may be easily deformed in a manufacturing process, and when the thickness of the first film is more than 500 ⁇ m, economic efficiency decreases.
- a thickness of the second film is not particularly limited either in an embodiment of the present invention.
- a thickness of the second film may be set to be the same as that of the first film.
- a thickness of the second film may be set to be relatively thinner than that of the first film.
- a thickness of the curable composition included in the adhesive film according to an embodiment of the present invention is not particularly limited, and may be properly selected according to the following conditions in consideration of a purpose of the applied film.
- a method of preparing the adhesive film as described above is not particularly limited.
- the method of preparing the adhesive film may include a first step in which a coating solution containing the curable composition described above is coated on the base film or the release film; and a second step in which the coating solution applied in the first step is dried.
- the method of preparing the adhesive film according to an embodiment of the present invention may further include a third step in which a base film or release film is additionally pressed onto the coating solution dried in the second step.
- the first step according to an embodiment of the present invention is a step of preparing a coating solution by dissolving or dispersing the curable composition described above in a proper solvent.
- a content of the epoxy resin or the like contained in the coating solution may be properly controlled depending on a purpose.
- Types of the solvent used for preparing the coating solution in an embodiment of the present invention are not particularly limited. However, when a drying time of the solvent is excessively prolonged or drying at high temperature is required, problems may occur in terms of workability or durability of the adhesive film, and thus the solvent having a volatilization temperature of 200° C. or less, 130° C. or less, or 100° C. or less may be preferably used.
- solvent examples include, but are not limited to, one type or mixtures of at least two types of methyl ethylketone (MEK), acetone, toluene, dimethyl formamide (DMF), methyl cellosolve (MCS), tetra-hydrofuran (THF), N-methyl pyrrolidone (NMP), ethyl cellosolve (ECS), etc.
- MEK methyl ethylketone
- MFS methyl cellosolve
- THF tetra-hydrofuran
- NMP N-methyl pyrrolidone
- ECS ethyl cellosolve
- a method of applying the coating solution as described above onto the base film or the release film in the first step according to an embodiment of the present invention is not particularly limited, and for example, knife coating, roll coating, spray coating, gravure coating, curtain coating, comma coating, lip coating, or the like may be used without limitation.
- the second step according to an embodiment of the present invention is a step of forming an adhesive layer containing the curable adhesive resin by drying the coating solution coated in the first step. That is, in the second step according to an embodiment of the present invention, the adhesive layer may be formed by heating, drying, and removing the coating solution applied onto the film.
- a drying condition is not particularly limited, and for example, the drying may be performed at a temperature in a range of 70 to 200° C. for 1 to 10 minutes.
- the method of preparing the adhesive film according to an embodiment of the present invention may further include the third step of pressing an additional base film or release film on the curable composition formed on the film following the second step.
- the additional release film or base film (cover film or second film) may be pressed through hot-roll laminating or a pressing process after the curable composition is coated onto the film.
- the third step may be performed by a hot-roll-laminating method to enable a continuous process and improve effectiveness, and the process may be performed at a temperature in a range of about 10 to 100° C. and a pressure in a range of about 0.1 to 10 kg/cm 2 .
- an organic electronic device including a substrate; an organic electronic element formed on the substrate; and the aforementioned adhesive film encapsulating the organic electronic element.
- the adhesive film may cover the entire surface of the organic electronic element.
- the organic electronic element may be an organic light emitting diode in an embodiment of the present invention.
- the organic electronic device may further include a protective layer protecting the organic electronic element between the adhesive film and the organic electronic element.
- a method of preparing an organic electronic device which includes applying the adhesive film containing the curable composition described above onto a substrate on which an organic electronic element is formed to cover the organic electronic element.
- the production method may further include a step of curing the adhesive film containing the curable composition.
- the step of applying the adhesive film onto the organic electronic element may be performed through a hot-roll laminating, heat press, or vacuum press method, but is not particularly limited.
- the step of applying the adhesive film onto the organic electronic element may be performed at a temperature in a range of 50 to 90° C., and the step of curing the adhesive film may be performed by heating to a temperature in a range of 70 to 110° C. or irradiating with UV rays.
- a transparent electrode is formed on a substrate 21 such as a glass or polymer film using a method such as vacuum deposition, sputtering, or the like, and an organic material layer is formed on the transparent electrode.
- the organic material layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and/or an electron transport layer.
- a second electrode is formed on the organic material layer.
- the adhesive film 12 described above is applied onto the upper part of the organic electronic element 23 of the substrate 21 to completely cover the organic electronic element 23.
- a method of applying the adhesive film 12 is not particularly limited, and for example, a cover substrate (e.g., glass or polymer film) 22 to which the curable composition of the adhesive film according to an embodiment of the present invention is transferred in advance may be applied on the upper part of the organic electronic element 23 formed on the substrate 21 using a method such as heating, pressing, etc.
- a transfer of the adhesive film 12 to the cover substrate 22 may be performed while applying heat using a vacuum press, a vacuum laminator, and the like after delaminating a base or release film formed on the film using the aforementioned adhesive film according to an embodiment of the present invention.
- a process temperature to be about 100° C. or less, and a process time to be within 5 minutes.
- a vacuum press or a vacuum laminator may also be used.
- a temperature condition in this step may be set as described above, and a process time is preferably within 10 minutes.
- an additional curing process may be performed with respect to the adhesive film to which the organic electronic element is pressed in an embodiment of the present invention.
- the curing process (primary curing) may be performed in a heat chamber or UV chamber.
- the condition of primary curing may be properly selected in consideration of stability of the organic electronic device.
- the manufacturing process described above is merely one example for encapsulating the organic electronic element according to an embodiment of the present invention, and the process order and the process conditions may be arbitrarily modified.
- an order of the transfer and press process in an embodiment of the present invention may be changed as a method in which the adhesive film 12 is transferred to the organic electronic element 23 on the substrate 21 first, and then the cover substrate 22 is pressed thereto. Further, after forming a protective layer on the organic electronic element 23 and applying the adhesive film 12 thereto, the applied adhesive film 12 may be cured without pressing the cover substrate 22 thereto and used.
- the encapsulating film may protect the element, prevent damage to the element from moisture contained in the composition, ionic substances, and other foreign substances, and effectively block electrochemical corrosion, and thus a lifespan and durability of the organic electronic device may be improved.
- FIG. 1 is a cross-sectional view illustrating an organic electronic device according to an embodiment of the present invention.
- the prepared solution was applied onto a release surface of a release PET film using a comma coater, and dried at 110° C. for 3 minutes, and then an adhesive film having a thickness of 20 ⁇ m was formed.
- An adhesive film was prepared in the same method as Example 1 except that a silane-modified epoxy resin (KSR-177) was added instead of the low-chlorine BPA type epoxy, and a silane coupling agent was not added.
- a silane-modified epoxy resin KSR-177
- An adhesive film was prepared in the same method as Example 1 except that C11ZA (SHIKOKU CHEMICALS CORPORATION) which starts to cure at a high temperature was added instead of the imidazole curing agent 2PZ.
- C11ZA SHIKOKU CHEMICALS CORPORATION
- An adhesive film was prepared in the same method as Example 1 except that an epoxy resin (Epiclon 840) was added instead of the low-chlorine BPA type epoxy, and 3 phr of a reactive dilution agent (PG-202; Kukdo Chemical Co., Ltd.) was added.
- an epoxy resin Epon 840
- 3 phr of a reactive dilution agent PG-202; Kukdo Chemical Co., Ltd.
- An adhesive film was prepared in the same method as Example 1 except that 2 parts by weight of a silane coupling agent was added with respect to 100 parts by weight of a resin, xylene was added instead of the methyl ethylketone as an organic solvent, and the applied solution was dried at 100° C. for 1 minute.
- Measurement device Purge & Trap sampler-GC/MSD system (P & T: JAI JTD-505III, GC/MS: Agilent 7890B/5977A)
- Samples of the films prepared in examples and comparative examples were weighed to about 50 mg, passed through purge and trap at 150° C. for 1 hour, and a total amount of VOCs was measured through GC-MS. The measured volatilization amount was quantified using toluene as a standard reagent.
- An element available for a lighting test was deposited on a glass substrate. After the adhesive film on a coated sheet was heat-laminated on the glass substrate for encapsulating, the film was vacuum-pressed for 3 minutes at a pressure of 5 kg/cm 2 while being heated at 80° C. on the substrate. The pressed sample was thermally cured at 100° C. for 2 hours in an oven. The thermally cured sample was observed under conditions of a constant temperature and humidity of 85° C. and 85% RH, and checked for dark spots. Through an observation for 300 hours, it was checked whether or not dark spots were generated on the sample.
- Example 1 in which the low-chlorine BPA type epoxy resin was used, and a small amount of the silane coupling agent was used, VOCs and ionic substances were both effectively suppressed.
- Example 2 in which a silane coupling agent was not included and the silane-modified epoxy resin was used, an amount of an alcoholic volatile material that caused significant damage to the organic elements was decreased.
- Example 3 in which the imidazole curing agent was changed, storing stability and heat stability in the process were improved by controlling a curing temperature while maintaining other conditions to be the same.
- Comparative Example 1 in which a generally used epoxy resin was used, a great amount of VOCs and ionic substances were generated, and in Comparative Example 2 in which 2 parts by weight of a silane coupling agent was used and xylene was used as an organic solvent, a great amount of VOCs were generated.
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
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Abstract
Description
X≤1,000 ppm [Equation 1]
Y≤1,000 ppm, [Equation 2]
-
- 12: adhesive film
- 21: substrate
- 22: cover substrate
- 23: organic electronic element
TABLE 1 | |||||
Ionic | Etc. (Wire | ||||
VOCs | substance | corrosion and | |||
(ppm) | (ppm) | Dark spot | bubbles) | ||
Example 1 | 193 | 510 | None | Good |
Example 2 | 156 | 675 | None | Good |
Example 3 | 164 | 509 | None | Good |
Comparative | 1183 | 1288 | Generated | Wire corrosion |
Example 1 | ||||
Comparative | 1567 | 555 | Generated | Bubbles formed on |
Example 2 | pressing/curing | |||
Claims (14)
X≤1,000 ppm [Equation 1]
Y≤1,000 ppm, [Equation 2]
Applications Claiming Priority (3)
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KR20130113532 | 2013-09-24 | ||
KR10-2013-0113532 | 2013-09-24 | ||
PCT/KR2014/008901 WO2015046880A1 (en) | 2013-09-24 | 2014-09-24 | Curable composition |
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EP (1) | EP2977406B1 (en) |
JP (1) | JP6350953B2 (en) |
KR (1) | KR101574023B1 (en) |
CN (1) | CN105073884B (en) |
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CN107851731B (en) * | 2015-06-09 | 2020-05-12 | 株式会社Lg化学 | Organic electronic device |
KR101805298B1 (en) * | 2016-03-22 | 2017-12-05 | 주식회사 케이씨씨 | Thermosetting adhesive flim |
CN114621634B (en) | 2016-12-09 | 2023-07-14 | 株式会社Lg化学 | Encapsulation composition, organic electronic device including the same, and method of manufacturing the same |
RU2755070C1 (en) * | 2017-12-29 | 2021-09-13 | Ксило Текнолоджиз АГ | Laminate with synchronous structure |
CN111205801A (en) * | 2020-01-17 | 2020-05-29 | 天津瑞宏汽车配件制造有限公司 | Low-halogen low-shrinkage epoxy resin liquid packaging material for integrated circuit manufacturing |
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US20150368528A1 (en) | 2015-12-24 |
CN105073884A (en) | 2015-11-18 |
TWI602892B (en) | 2017-10-21 |
EP2977406B1 (en) | 2024-01-24 |
JP6350953B2 (en) | 2018-07-04 |
JP2016531996A (en) | 2016-10-13 |
TW201529782A (en) | 2015-08-01 |
KR101574023B1 (en) | 2015-12-02 |
EP2977406A1 (en) | 2016-01-27 |
EP2977406A4 (en) | 2016-12-07 |
KR20150033581A (en) | 2015-04-01 |
CN105073884B (en) | 2018-01-30 |
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